The Top 40 Emcees of All Time (25-21)

Ice Cube’s bizarro cousin has never had the mainstream success that his relative has, but Del remains a cherished member of the hip-hop underground after twenty years in the game. With his slightly stoned (OK, very stoned flow) and free-associative lyrics, he is still one of the best to ever represent the Bay. At very least, he’s proof that there are some good-ass drugs in Northern California. Hey, wouldn’t you rather see Del as the harried dad in “Are We There Yet” than Ice Cube?

24. Ol’ Dirty Bastard

Representing: Staten Island by way of Brooklyn

Yeah, Russell Jones was a kook. But he was a fucking talented kook. If you gave Kool Keith access to a room full of (OTC as well as illegal) meds, you’d have the ODB (I actually struggled a bit with ranking Keith below a rapper he obviously influenced, but now I’m at peace with my decision.) This dude, quite frankly, did “offbeat” better than anyone and still had the talent to deliver an “oh shit!” line in just about every song (and in some cases, like “Brooklyn Zoo”, just about EVERY line is an “oh shit!” line). He was one of a kind and is truly missed.

23. Lauryn Hill

Representing: Newark, NJ

Possibly blessed with TOO much talent-maybe that explains why she went bonkers. She was easily the star attraction of The Fugees, outshining the gifted Wyclef Jean and Pras, who deserves a special place alongside Tito Jackson and Andrew Ridgeley in the “Why is That Guy in the Band?” Hall of Fame. Her skills are underplayed because she so obviously tried to fit into a group dynamic, but much like Michael Jackson and George Michael, L-Boogie was much too big a group. Even post-“Miseducation”, she’s dropped hot 16s on songs by Joss Stone and John Legend, and hope springs eternal that Ms. Hill will soon make it all the way back.

She’s also the ONLY female MC on this list. You’ve gotta have skills to hang with this group of guys.

22. Kool Moe Dee

Representing: Harlem

Best original school emcee ever (that had anything that can be considered a recording career). That leaves guys like Busy Bee and Grandmaster Caz out (who rarely if ever made *records*), but certainly places Moe Dee above guys like Melle Mel. Definitely a prototype MC, Moe Dee had an authoritative voice that was perfect for crowd-rocking and was able to switch flows better than any rapper of his generation. Hey, the man has written TWO books on emcee skills. I’m not gonna argue with him.

21. Big Punisher

Representing: The Bronx

Much like another emcee you’ll find further along (MUCH further along) on this list, Pun passed away before his full potential could be realized. However, based on his two studio albums (plus a Terror Squad group album), a sea of guest appearances and some excellent freestyles, it’s clear to see that Pun was in a class by himself. Hell, his influence (or quite possibly his ghostwriting) even turned Fat Joe into a respectable MC. The first solo Latino rapper to go Platinum had skills commensurate with his XXXXXXXXXL size (that was a guess). Needless to say, that’s a LOTTA skills.